Propylene Oxide → 1-(5-(Hydroxymethyl)-3-nitro-1H-pyrazol-1-yl)propan-2-ol

HRID 1411930Notes

Reaction equation

HRID 1411930 reaction equation
[N+:1]([C:4]1[CH:8]=[C:7]([CH2:9][OH:10])[NH:6][N:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:17][CH:18]1[CH2:20][O:19]1>ClCCl>[OH:10][CH2:9][C:7]1[N:6]([CH2:17][CH:18]([OH:19])[CH3:20])[N:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 10796Cesium carbonateHCID 178526711HCID 178526711, compound

Product 1

HCID 866844761-(5-(Hydroxymethyl)-3-nitro-1H-pyrazol-1-yl)propan-2-olYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with (3-nitro-1H-pyrazol-5-yl)methanol (0.57 g, 4.0 mmol), Cs2CO3 (261 mg, 0.8 mmol), and 2-methyloxirane (20 mL). The mixture was stirred at 30° C. for 2 days. The mixture was cooled to room temperature and diluted with dichloromethane (100 mL). The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 250a (0.40 g, 50%) as a white solid. MS-ESI: [M+H]+ 202.3

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe resulting mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography
  6. washeluting with 30:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-26d69908a6cb409584289f16c8aab690
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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